Straightforward synthesis of photoactive chalcogen functionalized benzimidazo[1,2-<i>a</i>]quinolines

Silva, Rodrigo Borges da; Coelho, Felipe Lange; Rodembusch, Fabiano Severo; Schwab, Ricardo S.; Schneider, Juliana M. F. M.; Rampon, Daniel S.; Schneider, Paulo H.

doi:10.1039/c9nj01948k

Cited by 23 publications

(14 citation statements)

References 55 publications

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“…SePh-functionalized derivatives are relevant to future probe design. It is a good paper on great and interesting novel compounds [30]. of the sulfur analogs.…”

Section: Selenium In Therapeutics Medicinal Chemistry and Skeleton Coresmentioning

confidence: 99%

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Discussions of Fluorescence in Selenium Chemistry: Recently Reported Probes, Particles, and a Clearer Biological Knowledge

et al. 2021

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In this review from literature appearing over about the past 5 years, we focus on selected selenide reports and related chemistry; we aimed for a digestible, relevant, review intended to be usefully interconnected within the realm of fluorescence and selenium chemistry. Tellurium is mentioned where relevant. Topics include selenium in physics and surfaces, nanoscience, sensing and fluorescence, quantum dots and nanoparticles, Au and oxide nanoparticles quantum dot based, coatings and catalyst poisons, thin film, and aspects of solar energy conversion. Chemosensing is covered, whether small molecule or nanoparticle based, relating to metal ion analytes, H2S, as well as analyte sulfane (biothiols—including glutathione). We cover recent reports of probing and fluorescence when they deal with redox biology aspects. Selenium in therapeutics, medicinal chemistry and skeleton cores is covered. Selenium serves as a constituent for some small molecule sensors and probes. Typically, the selenium is part of the reactive, or active site of the probe; in other cases, it is featured as the analyte, either as a reduced or oxidized form of selenium. Free radicals and ROS are also mentioned; aggregation strategies are treated in some places. Also, the relationship between reduced selenium and oxidized selenium is developed.

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“…SePh-functionalized derivatives are relevant to future probe design. It is a good paper on great and interesting novel compounds [30]. of the sulfur analogs.…”

Section: Selenium In Therapeutics Medicinal Chemistry and Skeleton Coresmentioning

confidence: 99%

“…It is a good paper on great and interesting novel compounds [30]. Some compounds containing selenium were intended for chemotherapy.…”

Section: Selenium In Therapeutics Medicinal Chemistry and Skeleton Coresmentioning

confidence: 99%

Discussions of Fluorescence in Selenium Chemistry: Recently Reported Probes, Particles, and a Clearer Biological Knowledge

et al. 2021

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“…These benzimidazole‐quinoline hybrid compounds are useful as they employ methods like molecular docking, NMR skeletons of biomolecules, and computer‐aided drug design to shorten research time as well as expenses [24] . Some benzimidazole[1,2‐a] quinoline have recently been discovered to have biologically intriguing properties [25] such as antimicrobial, antifungal, and antitumor [26] …”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, In Silico and In Vivo Evaluation of Benzimidazole‐Bearing Quinoline Schiff Bases as New Anticonvulsant Agents

et al. 2023

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Nitrogen‐containing hybrid heterocyclic compounds have been gaining attention in the field of drug discovery and development due to their diverse pharmacological activities and relatively low toxicity. This study aimed to synthesize a series of new quinoline‐bearing amino acid‐derived benzimidazole derivatives i. e. 3‐{[1‐(1H‐Benzoimidazol‐2‐yl)‐subsituted‐methyl}‐4a,8a‐ dihydro‐1H‐quinoline‐2‐one, and 3‐{[1‐(1H‐Benzoimidazol‐2‐yl)‐substituted‐methyl}‐3H‐ quinoline‐2‐thione. These compounds were synthesized by the condensation of 2‐oxo‐1,2‐dihydro‐quinoline‐3‐ carbaldehyde and 2‐the oxo‐1,2‐dihydro‐quinoline‐3‐carbaldehyde with various substituted 1‐(1H‐benzimidazole‐2‐yl)‐methylamine. After synthesizing the compound, it was subjected to various characterization techniques such as IR, 1HNMR, 13CNMR, and Mass spectroscopy. The synthesized compounds were evaluated for their potential as an anticonvulsant using the subcutaneous Pentylenetetrazol (scPTZ) method, and the results were compared with those obtained for phenytoin and carbamazepine, which were used as standard drugs. Among all the screened derivatives 4 d, 4 e, 5 a, and 5 b were found to be the most potent as compared to conventional drugs (phenytoin and carbamazepine). Also, the molecular docking analysis of the synthesized compounds showed that they share the same mechanism of action as phenytoin and carbamazepine, which involves the inhibition of voltage‐gated sodium channels. Additionally, the analysis revealed that these compounds also inhibit the NMDA receptor. Overall, the development of nitrogen‐containing hybrid heterocyclic compounds has the potential to significantly contribute to the discovery and development of new drugs with improved efficacy, selectivity, and safety profiles.

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“…In this sense and aiming our continuous interest in the synthesis of chalcogen compounds, − the present study describes a novel methodology involving in situ reduction of elemental selenium to generate a nucleophilic Se 2– species in superbasic media [KOH and dimethylsulfoxide (DMSO)] to produce 2,5-disubstituted photoactive selenophenes. The scope of the methodology was investigated using 1,3-diyne derivatives containing different substituents with electron-donating and electron-withdrawing features in different positions to verify electronic and steric effects.…”

Section: Introductionmentioning

confidence: 99%

Evidence of a Photoinduced Electron-Transfer Mechanism in the Fluorescence Self-quenching of 2,5-Substituted Selenophenes Prepared through In Situ Reduction of Elemental Selenium in Superbasic Media

et al. 2021

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A series of new 2,5-disubstituted selenophene derivatives are described from elemental selenium and 1,3-diynes in superbasic media. The activation of elemental selenium in a KOH/DMSO system allows cyclization with conjugated diynes at room temperature. The cyclization reaction is extended to a broad range of functional groups, for which photophysics were experimentally and theoretically investigated. The selenophene derivatives present absorption maxima in the UV-A region and fluorescence emission in the violet-toblue region. Fluorescence decay profiles were obtained showing a monoexponential decay with fast fluorescence lifetimes (∼0.118 ns), as predicted by the Strickler−Berg relations. In general, in both investigations, no dependence on the solvent polarity on the absorption and emission maxima location was observed. On the other hand, solvents and substituents are shown to play a role in the fluorescence quantum yield values. In addition, a fluorescence selfquenching behavior could be observed, related to a photoinduced electron-transfer mechanism. Theoretical calculations performed at the MP2/ADC(2)/cc-pVDZ level of theory were performed in order to investigate the photophysical features of this series of selenophene derivatives.

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Straightforward synthesis of photoactive chalcogen functionalized benzimidazo[1,2-a]quinolines

Abstract: A series of new organochalcogen derivatives of benzimidazo[1,2-a]quinolines were synthesized. Both sulfur and selenium derivatives presented similar photophysical properties with absorption in the UV region and fluorescence emission in the violet-blue.

Cited by 23 publications

References 55 publications

Discussions of Fluorescence in Selenium Chemistry: Recently Reported Probes, Particles, and a Clearer Biological Knowledge

Discussions of Fluorescence in Selenium Chemistry: Recently Reported Probes, Particles, and a Clearer Biological Knowledge

Synthesis, Characterization, In Silico and In Vivo Evaluation of Benzimidazole‐Bearing Quinoline Schiff Bases as New Anticonvulsant Agents

Evidence of a Photoinduced Electron-Transfer Mechanism in the Fluorescence Self-quenching of 2,5-Substituted Selenophenes Prepared through In Situ Reduction of Elemental Selenium in Superbasic Media

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